Formaldehyde → Tert-butyl 3-(methylamino)benzylcarbamate

HRID 1784922Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].C=O.[C:19]([BH3-])#N.[Na+]>>[CH3:19][NH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10]

Participants

Reactant 3

HCID 712Formaldehyde

HCID 5003444Sodium cyanoborohydride

HCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamate

Product 1

HCID 57763264Tert-butyl 3-(methylamino)benzylcarbamate

Procedure

Tert-butyl 3-aminobenzylcarbamate was converted to the target molecule following standard reductive amination conditions using formaldehyde and sodium cyanoborohydride.

Sources & evidence

ORD record: ord-fbc5cb693c1a4ee4ad60661f5959feb5
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504420B2

Reaction notes

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