Methanol → HCID 66960124, compound

HRID 1367744Notes

Reaction equation

HRID 1367744 reaction equation
[CH2:1]([C:3]1[C:19]([O:20][CH2:21][O:22][CH3:23])=[CH:18][C:17]2[CH2:16][CH2:15][CH:14]3[CH:6]([CH2:7][CH2:8][C:9]4([CH3:25])[CH:13]3[CH2:12][CH2:11][C:10]4=[O:24])[C:5]=2[CH:4]=1)[CH3:2].CO.[BH4-].[Na+]>C1COCC1>[CH2:1]([C:3]1[C:19]([O:20][CH2:21][O:22][CH3:23])=[CH:18][C:17]2[CH2:16][CH2:15][CH:14]3[CH:6]([CH2:7][CH2:8][C:9]4([CH3:25])[CH:13]3[CH2:12][CH2:11][CH:10]4[OH:24])[C:5]=2[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 66959816HCID 66959816, compound

Product 1

HCID 66960124HCID 66960124, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred, rt, solution of 2-Et-3-O-MOM estrone 52 (743 mg, 2.18 mmol) in THF (10 mL)/methanol (40 mL) solution was added sodium borohydride (76 mg, 2 mmol). After one hour the reaction was quenched by addition of ammonium chloride (2 mL of saturated solution), diluted with ethyl acetate (50 mL) and water (25 mL), the organic layer separated and washed with water, brine, dried and evaporated. Column chromatography (hexane/ethyl acetate gradient) gave the desired alcohol 53 as a clear colourless oil (650 mg) which showed δH (400 MHz, CDCl3, ref. TMS=0) 7.09 (1H, s, ArH), 6.78 (1H, s, ArH), 5.17 (2H, s, OCH2), 3.69-3.78 (1H, m, CHOH) 3.48 (3H, s, OMe), 2.78-2.86 (2H, m, 6-CH2), 2.61 (2H, q, J 7.4, CH2Me), 1.24-2.38 (13H, m), 1.19 (3H, t, J 7.4, CH2Me) and 0.77 (3H, s, 18-CH3).

Workup

  1. customAfter one hour the reaction was quenched by addition of ammonium chloride (2 mL of saturated solution)
  2. additiondiluted with ethyl acetate (50 mL) and water (25 mL)
  3. customthe organic layer separated
  4. washwashed with water, brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-7e6904d06397426f82cdae11a5972349
Source dataset
uspto-grants-2011_02
Patent number
US07893284B2

Reaction notes

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