Methanol → HCID 58550928, compound

HRID 2204250Notes

Reaction equation

HRID 2204250 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].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

3

Reactant 2

HCID 887MethanolHCID 58550946HCID 58550946, compound

Product 1

HCID 58550928HCID 58550928, compound

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

Sources & evidence

ORD record
ord-46b3a8bf715f4def89038d82d8098bc3
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

Loading…