Sodium borohydride → HCID 21973117, compound

HRID 1178857Notes

Reaction equation

HRID 1178857 reaction equation
C[CH:2]1[C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5][CH2:4][C:3]1([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH:12]=[O:13].[BH4-].[Na+]>CO>[CH2:10]1[CH2:9][O:8][C:7]2([CH2:6][CH2:5][CH2:4][C:3]([CH2:12][OH:13])([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:2]2)[O:11]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21973125HCID 21973125, compound

Product 1

HCID 21973117HCID 21973117, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3,3-ethylenedioxy-1-phenylcyclohexanecarbaldehyde (1.43 g, 5.81 mmol) in methanol (25 mL) at 0° C. was added sodium borohydride (221 mg) in portions, and the resulting suspension was stirred at room temperature overnight. The reaction was quenched with saturated sodium bicarbonate and methanol was removed under vacuum. The aqueous layer was extracted with dichloromethane 3 times. The combined organic layers were dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound as clear colorless sticky oil (1.25 g, 87% yield). 1H NMR (400 MHz, CDCl3) δ 1.48-1.81 (7H, m), 1.88 (1H, d, J=16 Hz), 2.06 (1H, d, J=12 Hz), 2.22 (1H, d, J=12 Hz), 3.73-4.06 (5H, m), 7.15-7.25 (2H, m), 7.31-7.38 (3H, m). HPLC purity (retention time): 85% (1.44 min, method C). MS: 271.40 (M+Na+).

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate and methanol
  2. customwas removed under vacuum
  3. extractionThe aqueous layer was extracted with dichloromethane 3 times
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-df2f3219ee714fdf979817f6f920e8c7
Source dataset
uspto-grants-2007_10
Patent number
US07276631B2

Reaction notes

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