Benzyl chloroformate → HCID 86599161, compound

HRID 2116078Notes

Reaction equation

C([CH:8]([CH:10]1[CH2:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:20]=3[O:27][CH3:28])[C:12]=2[O:11]1)[NH2:9])C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.Cl[C:39]([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40]>>[CH3:28][O:27][C:20]1[C:21]([O:25][CH3:26])=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]1[C:12]2[O:11][CH:10]([CH2:8][NH:9][C:39](=[O:40])[O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH2:14][C:13]=2[CH:15]=[CH:16][CH:17]=1

Participants

Reactant 3

HCID 10387Benzyl chloroformate

HCID 81531Diisopropylethylamine

HCID 68967924HCID 68967924, compound

Product 1

HCID 86599161HCID 86599161, compoundYield 91.2%

Procedure

Treatment of (±)-benzyl[7-(2,3-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (2.7 g, 8.39 mmol) with diisopropylethylamine (1.63 g, 12.59 mmol) and benzyl chloroformate (1.72 g, 10.07 mmol) generally according to the procedure described for Intermediate 12 provided 3.21 g (91%) of (±)-benzyl {[7-(2,3-dimethoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate as a colorless oil.

Sources & evidence

ORD record: ord-636f74c850cc48069b65e3f15a99d968
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

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