Sodium borohydride → HCID 66953749, compound

HRID 1424595Notes

Reaction equation

HRID 1424595 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][C:16]3([CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:20]3=[O:28])[CH2:15]1)=[O:13])[CH2:8]2.[BH4-].[Na+]>CO>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([N:14]1[CH2:19][CH2:18][CH2:17][C:16]3([CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH:20]3[OH:28])[CH2:15]1)=[O:13])[CH2:8]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66954058HCID 66954058, compound

Product 1

HCID 66953749HCID 66953749, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-(2-adamantyl)-1-oxo-1,3-dihydrospiro[indene-2,3′-piperidine]-1′-carboxamide (3.0 mg, 0.079 mmol) in MeOH (3 mL) was added NaBH4 (12 mg, 0.317 mmol) at 0° C. under nitrogen. The reaction mixture was stirred for 4 h under N2 at rt. The reaction mixture was evaporated to give a residue, which was purified by preparative HPLC to afford N-(2-adamantyl)-1-hydroxy-1,3-dihydrospiro[indene-2,3′-piperidine]-1′-carboxamide (12 mg, 40%). 1HNMR (CD3OD, 400 MHZ): δ=1.51-1.75 (m, 5H), 1.78˜1.81 (m, 4H), 1.82˜2.00 (m, 11H), 2.50 (m, 1H), 3.00 (d, 1H), 3.20 (m, 1H), 3.55 (m, 1H), 3.65 (m, 1H), 3.81 (s, 1H), 4.75 (s, 1H), 7.22 (m, 3H), 7.388 (m, 1H).

Workup

  1. customThe reaction mixture was evaporated
  2. customto give a residue, which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-03168a6c06e54aca82c021a94a3d9392
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

Loading…