Benzyl chloroformate → (+/-)-Benzyl {[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate

HRID 2116023Notes

Reaction equation

HRID 2116023 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[C:14]2[CH2:15][CH:16]([CH2:18][NH2:19])[O:17][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]>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[C:14]2[CH2:15][CH:16]([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)[O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 68963220(+/-)-1-[4-(2,6-Dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine

Product 1

HCID 86599132(+/-)-Benzyl {[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamateYield 95%

Procedure

Treatment of (±)-1-[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (1.2 g, 4.14 mmol) with diisopropylethylamine (0.803 g, 6.21 mmol) followed by benzyl chloroformate (0.848 g, 4.97 mmol) generally according to the procedure described for Intermediate 12 provided 1.52 g (95%) of (±)-benzyl {[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate as a colorless oil. Anal. calcd. for C25H25NO3: C, 77.49; H, 6.5; N, 3.61. Found: C, 76.66; H, 6.31; N, 3.44. Chiral HPLC separation of (±)-benzyl {[4-(2,6-dimethylphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (Chiralcel OD, ethanol) provided two fractions. Fraction 1 (Rt=4.818 min, Chiralcel OD, ethanol); Fraction 2 (Rt=6.985 min, Chiralcel OD, ethanol).

Sources & evidence

ORD record
ord-f9808b97e8cb4df79731e16cd3d7c158
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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