Acetic Acid → HCID 11067502, compound

HRID 1195232Notes

Reaction equation

HRID 1195232 reaction equation
[O:1]=[C:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[CH2:18][CH2:17][C@@:16]2([CH3:24])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH:14]=[O:15])[CH3:13])=[CH:3]1.O1CCCC1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[OH:15][CH2:14][C@@H:12]([C@@H:11]1[C@:16]2([CH3:24])[C@H:8]([C@H:7]3[C@H:19]([CH2:18][CH2:17]2)[C@:20]2([CH3:23])[C:4](=[CH:3][C:2](=[O:1])[CH2:22][CH2:21]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1)[CH3:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 11461614(20R)-3-Oxopregn-4-ene-20-carboxaldehyde

Product 1

HCID 11067502HCID 11067502, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (20R)-3-oxopregn-4-ene-20-carboxaldehyde (100 g, 305 mmol, commercially available from Upjohn) in 1500 ml ethanol and 250 ml tetrahydrofuran cooled to approximately 5° C. was added sodium borohydride (3.35 g, 89 mmol) portionwise to keep the temperature below 15° C. After 20 minutes, acetic acid (100 ml) was added and the mixture was concentrated to a slush on a rotary evaporator. The residue was then taken up in chloroform, successively washed with water and brine, then dried over sodium carbonate and concentrated to yield (20R)-20-hydroxymethyl-4-pregnen-3-one as a white solid (100 g, 100%).

Workup

  1. customthe temperature below 15° C
  2. concentrationthe mixture was concentrated to a slush on a rotary evaporator
  3. washsuccessively washed with water and brine
  4. dry with materialdried over sodium carbonate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6c2d0b69551343ae8e0bf586fb241c8b
Source dataset
uspto-grants-1992_05
Patent number
US05110939

Reaction notes

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