Benzyl chloroformate → (+/-)-Benzyl(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate

HRID 2115932Notes

Reaction equation

[C:1]1([C:7]2[C:12]3[CH2:13][CH:14]([CH2:16][NH2:17])[O:15][C:11]=3[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>>[CH2:31]([O:30][C:28](=[O:29])[NH:17][CH2:16][CH:14]1[CH2:13][C:12]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=[CH:10][C:11]=2[O:15]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Reactant 3

HCID 10387Benzyl chloroformate

HCID 81531Diisopropylethylamine

HCID 16226460(+)-1-(4-Phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine

Product 1

HCID 86601824(+/-)-Benzyl(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamateYield 70.3%

Procedure

Treatment of (±)-(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methanamine (0.622 g, 2.38 mmol) with diisopropylethylamine (0.447 g, 3.57 mmol) and benzyl chloroformate (0.462 g, 2.62 mmol) generally according to the procedure described for Intermediate 12 provided 0.601 g (70%) of (±)-benzyl(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate as a white solid. mp 132-134° C.; Anal. calcd. for C23H21NO3: C, 76.86H, 5.89; N, 3.90. Found: C, 75.98H, 5.80; N, 3.72. Chiral HPLC separation of (±)-benzyl(4-phenyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate (Chiralcel OD, ethanol:water 15:85) provided two fractions. Fraction 1 (Rt=6.651 min Chiralcel OD, ethanol:water 1:3); Fraction 2 (Rt=7.395 min, Chiralcel OD, ethanol:water 1:3).

Sources & evidence

ORD record: ord-57077b22afdc4570bf9706f5ab40fd97
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

Loading…