Methanol → HCID 67092835, compound

HRID 1261857Notes

Reaction equation

HRID 1261857 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH2:14][N:15]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[C@H:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH3:17])[CH2:12][O:11][CH2:10][C@@H:9]1[CH2:35][CH:36]=[CH2:37])=[O:7])([CH3:4])([CH3:3])[CH3:2].C12BC(CCC1)CCC2.CO.B1([O-])O[O:50]1.O.O.O.O.[Na+]>O1CCCC1.O>[C:1]([O:5][C:6]([N:8]1[C@@H:9]([CH2:35][CH2:36][CH2:37][OH:50])[CH2:10][O:11][CH2:12][C@H:13]1[CH2:14][N:15]([C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[C@H:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH3:17])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 789669-Borabicyclo(3.3.1)nonane2×HCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 67093010HCID 67093010, compound

Product 1

HCID 67092835HCID 67092835, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3S,5R)-3-allyl-5-{[benzyloxycarbonyl-((S)-1-tert-butoxycarbonyl-ethyl)-amino]-methyl}-morpholine-4-carboxylic acid tert-butyl ester (4.50 g, 8.68 mmol) in tetrahydrofuran (90 mL) was added 9-borabicyclo[3.3.1]nonane solution (0.5 M in tetrahydrofuran, 36.4 mL, 18.2 mmol) at 0° C., then after 21/2 h another portion of 9-borabicyclo[3.3.1]nonane solution (0.5 M in tetrahydrofuran, 20.8 mL, 10.4 mmol) was added. The reaction mixture was stirred for another 45 min at 0° C., then methanol (80 mL), water (115 mL) and sodium perborate tetrahydrate (37.3 g, 242 mmol) were added. After 90 min the ice bath was removed, then after stirring for 16 h the reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2; heptane-ethyl acetate gradient) afforded the title compound (3.76 g, 81%). Colourless gum, MS: 537.5 (M+H)+.

Workup

  1. customAfter 90 min the ice bath was removed
  2. stirringafter stirring for 16 h the reaction mixture
  3. customwas partitioned between ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c5330fca4e2b45d4b3995ec7dbcb062a
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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