Sodium borohydride → HCID 18595675, compound

HRID 1581065Notes

Reaction equation

HRID 1581065 reaction equation
C([O:4][C:5]1[CH:22]=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:23])[C@H:13]([O:24][C:25](=[O:27])[CH3:26])[CH2:12]4)[CH2:9][C@@H:8]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:7]=2[CH:6]=1)(=O)C.[BH4-].[Na+]>CO>[C:25]([O:24][C@@H:13]1[CH2:12][C@H:11]2[C@H:10]3[C@H:19]([CH2:18][CH2:17][C@:15]2([CH3:16])[C@H:14]1[OH:23])[C:20]1[CH:21]=[CH:22][C:5]([OH:4])=[CH:6][C:7]=1[C@H:8]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:9]3)(=[O:27])[CH3:26].[CH2:32]([O:31][C:29]([CH2:28][C@H:8]1[C:7]2[CH:6]=[C:5]([OH:4])[CH:22]=[CH:21][C:20]=2[C@@H:19]2[C@H:10]([C@H:11]3[C@@:15]([CH2:17][CH2:18]2)([CH3:16])[C@@H:14]([OH:23])[C@H:13]([OH:24])[CH2:12]3)[CH2:9]1)=[O:30])[CH3:33]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18595679HCID 18595679, compound

Product 2

HCID 18595675HCID 18595675, compoundHCID 18595691HCID 18595691, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

300 mg. of 3,16α-diacetoxy-6β-ethoxycarbonylmethyl-1,3,5(10)-estratrien-17-one is dissolved in 11 ml. of methanol and gradually combined at +5°C. with 0.17 g. of NaBH4 in 9 ml. of methanol. After allowing the mixture to stand for 20 hours at room temperature, it is concentrated and stirred into water which contains hydrochloric acid. The reduction product is taken up in ethyl acetate, the solution is washed neutral, dried, and evaporated. By preparative thin-layer chromatography, 330 mg. of crude product yields 16α-acetoxy-6β-ethoxycarbonylmethyl-1,3,5(10)-estratriene-3,17β-diol, m.p. 170.5°-171.5°C. and 6β-ethoxycarbonylmethyl-1,3,5(10)-estratriene-3,16α,17β-triol, m.p. 192.5°-193°C.

Workup

  1. customgradually combined at +5°C. with 0.17 g
  2. concentrationit is concentrated
  3. washthe solution is washed neutral
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-6b476805ce7240e7afc0d778ed72204c
Source dataset
uspto-grants-1976_01
Patent number
US03935245

Reaction notes

Loading…