Sodium borohydride → HCID 58550928, compound

HRID 1908155Notes

Reaction equation

HRID 1908155 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13]([N:15]2[CH2:20][CH2:19][C:18]3([O:25][C:24]4[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=4[N:22]4[CH:30]=[CH:31][CH:32]=[C:21]34)[CH2:17][CH2:16]2)=[O:14])=[CH:7][C:4]=1[CH:5]=[O:6].[BH4-].[Na+]>CO>[OH:6][CH2:5][C:4]1[C:3]([O:2][CH3:1])=[CH:10][C:9]([O:11][CH3:12])=[C:8]([C:13]([N:15]2[CH2:16][CH2:17][C:18]3([O:25][C:24]4[CH:26]=[CH:27][CH:28]=[CH:29][C:23]=4[N:22]4[CH:30]=[CH:31][CH:32]=[C:21]34)[CH2:19][CH2:20]2)=[O:14])[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58550946HCID 58550946, compound

Product 1

HCID 58550928HCID 58550928, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,4-Dimethoxy-5-(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-ylcarbonyl)benzaldehyde (65 mg, 0.15 mmol) was suspended in MeOH (1 mL). NaBH4 (60 mg, 1.6 mmol) was added and the reaction mixture was allowed to stir for 15 minutes. The reaction mixture was filtered and was then purified by reverse phase preparative liquid chromatography utilizing a gradient of 20-99% methanol in water containing no modifier to give (5-(hydroxymethyl)-2,4-dimethoxyphenyl)(spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)methanone. ESI-MS m/z calc. 434.2. found 435.5 (M+1)+; Retention time: 1.63 minutes (3 min run).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customwas then purified by reverse phase preparative liquid chromatography

Sources & evidence

ORD record
ord-6f2a8843722b46e1839ac9767cb8d705
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

Loading…