Sodium borohydride → (4-Mercapto-adamantan-1-yl)-carbamic acid benzyl ester

HRID 2092646Notes

Reaction equation

HRID 2092646 reaction equation
[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([C:14]3=[S:21])[CH2:12]1)[CH2:18]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9](=[O:22])[NH:10][C:11]12[CH2:12][CH:13]3[CH2:19][CH:17]([CH2:16][CH:15]([CH:14]3[SH:21])[CH2:20]1)[CH2:18]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58192775HCID 58192775, compound

Product 1

HCID 58192789(4-Mercapto-adamantan-1-yl)-carbamic acid benzyl esterYield 50.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ketone 10B (100 mg, 0.317 mmol) in 5 ml of absolute MeOH was added NaBH4 (23 mg, 0.62 mmol) in portions at 0° C. The reaction was stirred for 1 h, at which time the solution was carefully quenched with water. The reaction mixture was extracted with EtOAc twice and the organic phases were combined, dried (anhydrous Na2SO4), and concentrated. The crude mixture was purified by column chromatography (0˜10% MeOH in EtOAc) to yield 51 mg of the desired mixture of alcohols 11A LC-MS (ESR): m/z=318 (M+H)+.

Workup

  1. customwas carefully quenched with water
  2. extractionThe reaction mixture was extracted with EtOAc twice
  3. dry with materialdried (anhydrous Na2SO4)
  4. concentrationconcentrated
  5. customThe crude mixture was purified by column chromatography (0˜10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-a795345d49f84c7987bceca06ecf19b1
Source dataset
uspto-grants-2013_05
Patent number
US08440720B2

Reaction notes

Loading…