Sodium borohydride → HCID 58551453, compound

HRID 2204261Notes

Reaction equation

HRID 2204261 reaction equation
[BH4-].[Na+].[CH2:3]([C:5]1[CH:32]=[CH:31][C:8]([C:9]([N:11]2[CH2:30][CH2:29][C:14]3([C:19]4=[CH:20][CH:21]=[CH:22][N:18]4[C:17]4[CH:23]=[CH:24][C:25]([C:27]#[N:28])=[CH:26][C:16]=4[O:15]3)[CH2:13][CH2:12]2)=[O:10])=[CH:7][C:6]=1[O:33][CH3:34])[CH3:4]>CO.O.O.O.O.O.O.Cl[Co]Cl>[NH2:28][CH2:27][C:25]1[CH:24]=[CH:23][C:17]2[N:18]3[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]3([CH2:29][CH2:30][N:11]([C:9]([C:8]4[CH:31]=[CH:32][C:5]([CH2:3][CH3:4])=[C:6]([O:33][CH3:34])[CH:7]=4)=[O:10])[CH2:12][CH2:13]3)[O:15][C:16]=2[CH:26]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 58551123HCID 58551123, compound

Product 1

HCID 58551453HCID 58551453, compound

Reagents, catalysts & solvents 2

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolvent

Procedure

NaBH4 (17.7 mg, 0.47 mmol) was slowly added to a solution of 1-(4-ethyl-3-methoxy-benzoyl)spiro[piperidine-4,4′-pyrrolo[2,1-c][1,4]benzoxazine]-7′-carbonitrile (20 mg, 0.050 mmol) and dichlorocobalt hexahydrate (22 mg, 0.090 mmol) in MeOH (1 mL) and was stirred at room temperature for 10 minutes. The reaction mixture was filtered and purified by reverse phase LC-MS (10-99% CH3CN/H2O) to yield (7-(aminomethyl)spiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-ethyl-3-methoxyphenyl)methanone. ESI-MS m/z calc. 431.5, found 432.5 (M+1)+; Retention time: 1.44 minutes (3 min run).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified by reverse phase LC-MS (10-99% CH3CN/H2O)

Sources & evidence

ORD record
ord-79abfe8597e7450aa7291835e44300af
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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