Borane → HCID 58610165, compound

HRID 1592830Notes

Reaction equation

HRID 1592830 reaction equation
B.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]([OH:24])[C@H:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:11]2=O)=[CH:5][CH:4]=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([C@@H:32]([OH:47])[C@@H:33]2[O:38][CH2:37][CH2:36][N:35]([CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]2=O)=[CH:28][CH:27]=1>O1CCCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]([C@@H:10]2[O:15][CH2:14][CH2:13][N:12]([CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:11]2)[OH:24])=[CH:7][CH:8]=1.[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([C@@H:32]([C@H:33]2[O:38][CH2:37][CH2:36][N:35]([CH2:39][C:40]3[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:34]2)[OH:47])=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 6331BoraneHCID 58610175HCID 58610175, compoundHCID 58610187HCID 58610187, compound

Product 2

HCID 58610165HCID 58610165, compoundHCID 58610166HCID 58610166, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of borane in tetrahydrofuran (1M, 29 ml) was added dropwise to a stirred solution of diastereomer 1 (2R)-2-[(S)-(4-chlorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one and (2S)-2-[(R)-(4-chlorophenyl)(hydroxy)methyl]-4-benzylmorpholin-3-one (2.40 g 7.24 mmol) in dried tetrahydrofuran (30 ml) at room temperature under nitrogen causing effervesence. The solution was heated to 60° C. for 2 h, allowed to cool to room temperature and excess borane quenched by adding methanol (14 ml) slowly. Aqueous hydrochloric acid (1M, 14 ml) was added, heated to 60° C. for 1 h and then evaporated to a white solid. Added saturated aqueous sodium carbonate (50 ml) and diethyl ether (50 ml) to dissolve the solid and extracted with diethyl ether (2×50ml). The extracts were washed with brine solution, dried, filtered and evaporated to a colourless oil (2.38 g). The oil was purified by chromatography on silica eluting with diethyl ether:hexane 75:25 to give (R)-[4-chlorophenyl][(2R)-4-benzylmorpholin-2-yl]methanol and (S)-[4-chlorophenyl][(2S)-4-benzylmorpholin-2-yl]methanol as a colourless oil (2.08 g)

Workup

  1. temperatureto cool to room temperature
  2. customexcess borane quenched
  3. additionby adding methanol (14 ml) slowly
  4. additionAqueous hydrochloric acid (1M, 14 ml) was added
  5. temperatureheated to 60° C. for 1 h
  6. customevaporated to a white solid
  7. dissolutionAdded saturated aqueous sodium carbonate (50 ml) and diethyl ether (50 ml) to dissolve the solid
  8. extractionextracted with diethyl ether (2×50ml)
  9. washThe extracts were washed with brine solution
  10. customdried
  11. filtrationfiltered
  12. customevaporated to a colourless oil (2.38 g)
  13. customThe oil was purified by chromatography on silica eluting with diethyl ether:hexane 75:25

Sources & evidence

ORD record
ord-d341f4a966664d598e28bc385c87a103
Source dataset
uspto-grants-2007_11
Patent number
US07294623B2

Reaction notes

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