Benzyl chloroformate → HCID 86599097, compound

HRID 2116036Notes

Reaction equation

HRID 2116036 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[O:16][CH:15]([CH2:18][NH2:19])[CH2:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C(N(C(C)C)CC)(C)C.Cl[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33]>>[CH2:35]([O:34][C:32](=[O:33])[NH:19][CH2:18][CH:15]1[CH2:14][C:13]2[CH:12]=[CH:11][CH:10]=[C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:20])([F:1])[F:21])[CH:4]=3)[C:17]=2[O:16]1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11960863(+/-)-[7-(3-Trifluoromethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

Product 1

HCID 86599097HCID 86599097, compoundYield 97.1%

Procedure

Treatment of (±)-1-{7-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methanamine (1.67 g, 5.06 mmol) with diisopropylethylamine (0.98 g, 7.59 mmol) followed by benzyl chloroformate (1.04 g, 7.59 mmol) generally according to the procedure described for Intermediate 12 provided 2.1 g (97%) of (±)-benzyl({7-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methyl)carbamate as a colorless oil. Anal. calcd. for C24H20F3NO3: C, 67.44; H, 4.72; N, 3.28. Found: C, 67.08; H, 5.05; N, 3.22. Chiral HPLC separation of (±)-benzyl ({7-[3-(trifluoromethyl)phenyl]-2,3-dihydro-1-benzofuran-2-yl}methyl)carbamate (Chiralpak OJ, isopropanol:carbon dioxide 15:85) provided two fractions. Fraction 1 (Rt=6.12 min, Chiralpak OJ, isopropanol:carbon dioxide 15:85); Fraction 2 (Rt=7.17 min, Chiralpak OJ, isopropanol:carbon dioxide 15:85).

Sources & evidence

ORD record
ord-cd068f4a87d641849ecd4ba59552e6ba
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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