tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidate → {4-[(5,6,7,8-Tetrahydro-quinolin-7-ylamino)-methyl]-benzyl}-carbamic acid tert-butyl ester

HRID 2308290Notes

Reaction equation

HRID 2308290 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N:18]1[C:27]2[CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:28][CH:25]2[CH2:26][C:27]3[N:18]=[CH:19][CH:20]=[CH:21][C:22]=3[CH2:23][CH2:24]2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateHCID 4311764Sodium borohydrideHCID 148359725,6,7,8-Tetrahydroquinolin-7-amine

Product 1

HCID 68900505{4-[(5,6,7,8-Tetrahydro-quinolin-7-ylamino)-methyl]-benzyl}-carbamic acid tert-butyl esterYield 100.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using general procedure B: Reaction of (4-Formyl-benzyl)-carbamic acid tert-butyl ester (356 mg, 1.51 mmol), 5,6,7,8-Tetrahydro-quinolin-7-ylamine (224 mg, 1.51 mmol) in anhydrous MeOH (5 mL) at room temperature overnight under N2 and 2 min of stirring after addition of sodium borohydride (115 mg, 3.00 mmol), followed by purification of crude material using chromatography on silica gel (2:2:96 CH3OH—NH3 H2O—CH2Cl2) afforded the title compound (556 mg, 100%) as a white foam.

Workup

  1. customfollowed by purification of crude material

Sources & evidence

ORD record
ord-6b807171eb2c40879a9ad90bbdbf77c2
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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