tert-butyl N-(pyrrolidin-3-yl)carbamate → HCID 67353744, compound

HRID 1673150Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([C:19]([NH2:21])=[O:20])[C:5]2[N:9]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH:16]=O)=[CH:12][CH:11]=3)[NH:7][C:6]=2[CH:18]=1.[C:22]([O:26][C:27]([NH:29][CH:30]1[CH2:34][CH2:33][NH:32][CH2:31]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].C([BH3-])#N.[Na+]>[Cl-].[Zn+2].[Cl-].CO.CN(C=O)C>[NH2:21][C:19]([C:4]1[C:5]2[N:9]=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16][N:32]4[CH2:33][CH2:34][CH:30]([NH:29][C:27](=[O:28])[O:26][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:31]4)=[CH:12][CH:11]=3)[NH:7][C:6]=2[CH:18]=[CH:2][CH:3]=1)=[O:20]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of EXAMPLE 7B (300 mg, 1.13 mmol) and 3-(tert-butoxycarbonylamino)pyrrolidine (631 mg, 3.39 mmol) in 1:1 methanol/N,N′-dimethylformamide (20 mL) was stirred at ambient temperature for 2 hours. Sodium cyanoborohydride (213 mg, 3.39 mmol) and zinc chloride (154 mg, 1.13 mmol) were added and the mixture stirred at 50° C. for 18 hours. The mixture was concentrated and the residue purified by HPLC (Zorbax C-8, 0.1% trifluoroacetic acid/acetonitrile/water) to provide the title compound (415 mg, 84%). MS (DCI/NH3) m/z 436 (M+H)+.

Workup

concentrationThe mixture was concentrated
customthe residue purified by HPLC (Zorbax C-8, 0.1% trifluoroacetic acid/acetonitrile/water)

Sources & evidence

ORD record: ord-2295b3c6ceb74049a77f51e8586190ca
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999117B2

Reaction notes

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