Benzyl chloroformate → HCID 86599134, compound

HRID 2116033Notes

Reaction equation

HRID 2116033 reaction equation
[CH3:1][O:2][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:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:17]3[O:16][CH:15]([CH2:18][NH:19][C:30](=[O:31])[O:32][CH2:33][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH2:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11960862HCID 11960862, compound

Product 1

HCID 86599134HCID 86599134, compoundYield 90%

Procedure

Treatment of (±)-1-[7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (2.4 g, 9.4 mmol) with diisopropylethylamine (1.82 g, 14.10 mmol) followed by benzyl chloroformate (1.92 g, 11.28 mmol) generally according to the procedure described for Intermediate 12 provided 3.28 g (90%) of (±)-benzyl {[7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate as a colorless oil. Rf=0.51 (silica, ethyl acetate:hexanes 2:8); Anal. calcd. for C24H23NO4: C, 74.02; H, 5.95; N, 3.6. Found: C, 73.52; H, 6.06; N, 3.28. Chiral HPLC separation of (±)-benzyl {[7-(3-methoxyphenyl)-2,3-dihydro-1-benzofuran-2-yl]methyl}carbamate (Chiralpak OD, ethanol) provided two fractions. Fraction 1 (Rt=6.220 min, Chiralpak OD, ethanol); Fraction 2 (Rt=8.373 min, Chiralpak OD ethanol).

Sources & evidence

ORD record
ord-77d2489bdc624ec5be809c0ced8a3811
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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