Thionyl Chloride → (S)-benzyl 5-(chloromethyl)-2,3-dihydro-1H-inden-2-ylcarbamate

HRID 473105Notes

Reaction equation

HRID 473105 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@H:7]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6]2.S(Cl)([Cl:25])=O>C(Cl)Cl>[Cl:25][CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C@H:7]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:6]2

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 70224068(S)-benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamate

Product 1

HCID 70223052(S)-benzyl 5-(chloromethyl)-2,3-dihydro-1H-inden-2-ylcarbamateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (S)-benzyl 5-(hydroxymethyl)-2,3-dihydro-1H-inden-2-ylcarbamate (5.72 mmol, 1.7 g) was added DCM (34.9 mL) followed by sulfurous dichloride (11.43 mmol, 1.360 g). The reaction was stirred for one hour before removing the solvent in vacuo. DCM was added (5 mL) before removing the solvent in vacuo, this procedure was followed a further twice to give a yellow solid (1.8 g, 100%). 1H NMR (400 MHz, CDCl3) δ 2.81 (m, 2H), 3.30 (m, 2H), 4.56 (m, 3H), 4.95 (brs, 1H), 5.12 (s, 2H), 7.19 (d, 2H), 7.25 (m, 1H), 7.33 (m, 5H).

Workup

  1. custombefore removing the solvent in vacuo
  2. additionDCM was added (5 mL)
  3. custombefore removing the solvent in vacuo

Sources & evidence

ORD record
ord-141452e01bd247e4af51c9a6e0c33da5
Source dataset
uspto-grants-2014_01
Patent number
US08633237B2

Reaction notes

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