Benzyl chloroformate → HCID 86599133, compound

HRID 2115967Notes

Reaction equation

HRID 2115967 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[O:15][CH:14]([CH2:17][NH2:18])[CH2:13][C:12]=3[CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.Cl[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30]>>[CH2:32]([O:31][C:29](=[O:30])[NH:18][CH2:17][CH:14]1[CH2:13][C:12]2[CH:11]=[CH:10][CH:9]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[C:16]=2[O:15]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 11960770HCID 11960770, compound

Product 1

HCID 86599133HCID 86599133, compoundYield 94%

Procedure

Treatment of (±)-[7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanamine (0.798 g, 2.856 mmol) with diisopropylethylamine (0.554 g, 4.286 mmol) and benzyl chloroformate (0.536 g, 3.143 mmol) generally according to the procedure described for Intermediate 12 afforded 1.01 g (94%) of (±)-benzyl[7-(3-fluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methylcarbamate as a white solid. Rf=0.40 (silica, ethyl acetate:hexanes 1:4); Anal. Calcd. for C23H20FNO3: C, 73.2; H, 5.34; N, 3.71. Found: C, 92.96; H, 5.38; N, 3.59.

Sources & evidence

ORD record
ord-47a35a13969345538505c6686029b7fd
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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