Sodium borohydride → HCID 66953995, compound

HRID 1424619Notes

Reaction equation

HRID 1424619 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([O:24][CH3:25])[CH:23]=1)[CH2:6][NH:7][C:8]([C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([C:13]3=[O:20])[CH2:11]1)[CH2:17]2)=[O:9].[BH4-].[Na+]>CO>[CH3:25][O:24][C:22]1[CH:21]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[CH:23]=1)[CH2:6][NH:7][C:8]([C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH:13]3[OH:20])[CH2:11]1)[CH2:17]2)=[O:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66954283HCID 66954283, compound

Product 1

HCID 66953995HCID 66953995, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(3,5-dimethoxybenzyl)-4-oxoadamantane-1-carboxamide (230 mg, 0.670 mol) in anhydrous CH3OH was added NaBH4 (100 mg, 2.7 mmol) at 0° C. The reaction mixture was stirred for 1 h at rt. The solvent was removed under reduced pressure, diluted with CH2Cl2 and washed with water. The organic layer was separated, dried, and concentrated to give N-(3,5-dimethoxybenzyl)-4-hydroxyadamantane-1-carboxamide (230 mg, 100%). 1H NMR: (400 MHz, CDCl3): δ=1.40 (d, 1H), 1.46-1.62 (m, 6H), 1.70-1.82 (m, 5H), 1.84-1.95 (m, 3H) 2.01-2.14 (m, 2H), 3.75 (s, 3H), 3.80 (s, 3H), 3.82 (s, 1H), 4.29 (d, 2H), 5.98 (s, 1H), 6.40 (m, 0.2H), 7.08 (d, 1H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additiondiluted with CH2Cl2
  3. washwashed with water
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-493641b3b7fd430d917392cf80011175
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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