Benzyl chloroformate → (+/-)-Benzyl {[7-(2,6-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate

HRID 2116047Notes

Reaction equation

HRID 2116047 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:17]2[O:16][CH:15]([CH2:18][NH2:19])[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1.C(N(C(C)C)CC)(C)C.Cl[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:17]2[O:16][CH:15]([CH2:18][NH:19][C:30](=[O:31])[O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:14][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11961030(+/-)-1-[7-(2,6-Difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

Product 1

HCID 86599138(+/-)-Benzyl {[7-(2,6-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamateYield 98.8%

Procedure

Treatment of (±)-1-[7-(2,6-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (1.54 g, 5.17 mmol) with diisopropylethylamine (1.02 g, 7.76 mmol) and benzyl chloroformate (0.971 g, 5.69 mmol) generally according to the procedure described for Intermediate 12 gave 2.02 g (98%) of (±)-benzyl {[7-(2,6-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate as a colorless oil. Anal. calcd. for C23H19F2NO3: C, 69.87; H, 4.84; N, 3.54. Found C, 69.54; H, 4.87; N, 3.31.

Sources & evidence

ORD record
ord-82526f8a37da4a699968e757f03f89bb
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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