Cyclohexanone → HCID 70479340, compound

HRID 615191Notes

Reaction equation

HRID 615191 reaction equation
[C:1]([BH3-])#N.[Na+].[C:5]1(=O)CCCC[CH2:6]1.Cl.[OH:13][C@H:14]1[CH2:31][C@@:30]2([CH3:32])[C@@H:17]([CH2:18][CH2:19][C@@H:20]3[C@@H:29]2[C@H:28]([NH:33][CH2:34][CH2:35][CH:36](C)[CH3:37])[CH2:27][C@@:25]2([CH3:26])[C@H:21]3[CH2:22][CH2:23][C@@H:24]2[C:39]([OH:41])=[O:40])[CH2:16][C@@H:15]1[OH:42]>C(O)C.C([O-])(O)=O.[Na+].C(OCC)(=O)C>[CH:34]1([NH:33][C@@H:28]2[CH2:27][C@@:25]3([CH3:26])[C@@H:21]([CH2:22][CH2:23][C@@H:24]3[C:39]([O:41][CH3:1])=[O:40])[C@H:20]3[C@H:29]2[C@:30]2([CH3:32])[C@@H:17]([CH2:18][CH2:19]3)[CH2:16][C@H:15]([OH:42])[C@@H:14]([OH:13])[CH2:31]2)[CH2:6][CH2:5][CH2:37][CH2:36][CH2:35]1

Participants

7

Reactant 3

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 70479606HCID 70479606, compound

Product 1

HCID 70479340HCID 70479340, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Sodium cyanoborohydride (2.0 g) and cyclohexanone (2.0 ml) were added to a solution of Intermediate 2 (2.0 g) in ethanol (30 ml) and the mixture was stirred for 24 h. The mixture was diluted with NaHCO3 solution and extracted with ethyl acetate (3×). The extract was washed with water, dried and evaporated to give a solid. This was dissolved in ethyl acetate and extracted with dilute hydrochloric acid (3×) and water (2×). These extracts were brought to pH 10 with 0.88 NH3 solution and then extracted with ethyl acetate (3×). The ethyl acetate extract was washed with water, dried and evaporated to give a solid. This was purified by crystallisation from ethyl acetate to give the title compound (1.67 g), m.p. 199°-202°, [α]D +6.5°.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. washThe extract was washed with water
  3. customdried
  4. customevaporated
  5. customto give a solid
  6. extractionextracted with dilute hydrochloric acid (3×) and water (2×)
  7. extractionextracted with ethyl acetate (3×)
  8. extractionThe ethyl acetate extract
  9. washwas washed with water
  10. customdried
  11. customevaporated
  12. customto give a solid
  13. customThis was purified by crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-25e85e541c03437e83f74c91d2c3e1d2
Source dataset
uspto-grants-1985_02
Patent number
US04497805

Reaction notes

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