Sodium borohydride → HCID 58551453, compound

HRID 1908165Notes

Reaction equation

HRID 1908165 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-4de43451049748ad8d3bd961dd26782a
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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