Methanol → HCID 12837427, compound

HRID 2058441Notes

Reaction equation

HRID 2058441 reaction equation
[C:1]([CH:9]1[C:29](=[O:30])[CH2:28][CH2:27][C@@:26]2([CH3:31])[C@H:10]1[CH2:11][CH2:12][C@@H:13]1[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:32])[C@H:14]1[CH2:15][CH2:16][C@@H:17]2[C@H:18]([CH:20]=[O:21])[CH3:19])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>O1CCCC1.CCOCC>[C:1]([CH:9]1[C:29](=[O:30])[CH2:28][CH2:27][C@@:26]2([CH3:31])[C@H:10]1[CH2:11][CH2:12][C@@H:13]1[C@@H:25]2[CH2:24][CH2:23][C@@:22]2([CH3:32])[C@H:14]1[CH2:15][CH2:16][C@@H:17]2[C@@H:18]([CH3:19])[CH2:20][OH:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 54325637HCID 54325637, compound

Product 1

HCID 12837427HCID 12837427, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

The (5α,20R)-4-benzoyl-3-oxopregnane-20-carboxaldehyde (436 mg, 1.0 mmole) in tetrahydrofuran:methanol (2.0 ml, 1:1) is mixed with sodium borohydride (9.5 mg, 0.25 mmole) at 0° C. for 1 hours. The mixture is then diluted with ether and washed with 0.5 N hydrochloric acid and brine and then dried and the solvent is evaporated to leave, as a resiue, (5α,20R)-4-benzoyl-21-hydroxy-20 -methylpregnan-3-one.

Workup

  1. washwashed with 0.5 N hydrochloric acid and brine
  2. customdried
  3. customthe solvent is evaporated

Sources & evidence

ORD record
ord-5c1b8e3058744a84b30a72c1aa8cc9eb
Source dataset
uspto-grants-1982_03
Patent number
US04317817

Reaction notes

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