Sodium borohydride → HCID 58550924, compound

HRID 1908172Notes

Reaction equation

HRID 1908172 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:29]3[C:30]([CH:33]=[O:34])=[CH:31][CH:32]=[C:28]3[C:8]3([CH2:13][CH2:12][N:11]([C:14](=[O:27])[C:15]4[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[C:17]([O:25][CH3:26])[CH:16]=4)[CH2:10][CH2:9]3)[O:7][C:6]=2[CH:35]=1.[BH4-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:29]3[C:30]([CH2:33][OH:34])=[CH:31][CH:32]=[C:28]3[C:8]3([CH2:13][CH2:12][N:11]([C:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:24])[F:23])=[C:17]([O:25][CH3:26])[CH:16]=4)=[O:27])[CH2:10][CH2:9]3)[O:7][C:6]=2[CH:35]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58550852HCID 58550852, compound

Product 1

HCID 58550924HCID 58550924, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

7-Chloro-1′-(3-methoxy-4-(trifluoromethyl)benzoyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1-carbaldehyde (50 mg, 0.10 mmol) dissolved in dry THF (3 mL) was cooled to 0° C. NaBH4 (3.9 mg, 0.10 mmol) was added and stirring was continued for 30 min. The mixture was filtered through Celite, evaporated and purified by column chromatography (5-30% AcOEt in dichloromethane) to yield (7-chloro-1-(hydroxymethyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(3-methoxy-4-(trifluoromethyl)phenyl)methanone. ESI-MS m/z calc. 506.9. found 507.0 (M+1)+; Retention time: 1.96 minutes (3 min run).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated
  3. custompurified by column chromatography (5-30% AcOEt in dichloromethane)

Sources & evidence

ORD record
ord-954132295919426b840445a060faf657
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

Loading…