Benzyl chloroformate → Benzyl 7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-ylcarbamate

HRID 1672541Notes

Reaction equation

HRID 1672541 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].CC[N:14]([CH:18]([CH3:20])[CH3:19])C(C)C.[OH-:21].[Na+]>C(Cl)Cl>[OH:21][CH:10]1[CH2:11][C:19]2[C:18]([NH:14][C:2](=[O:3])[O:4][CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:20][CH:5]=[CH:6][C:7]=2[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 81531Diisopropylethylamine

Product 1

HCID 66696602Benzyl 7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-ylcarbamateYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzyl chloroformate (5.84 mL, 41.1 mmol) in 5 mL CH2Cl2 was added dropwise via addition funnel to Example 24A (3.05 g, 18.7 mmol) and Hunig's base (8.14 mL, 46.7 mmol) in dichloromethane (55 mL) at ambient temperature. After 18 hr IN (aq) NaOH solution (50 mL) was added and the reaction was stirred vigorously for 15 min. The separated organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was triturated with diethyl ether and the solid collected by suction filtration. The result was 3.37 g (61% yield) of the title compound as a brown solid. 1H NMR (300 MHz, DMSO-d6) δ 8.82 (s, 1H), 7.30-7.45 (m, 5H), 7.14 (m, 1H), 7.05 (t, 1H), 6.90 (m, 1H), 5.12, (s, 2H), 4.77 (d, 1H), 3.87 (m, 1H), 2.86 (m, 2H), 2.71 (m, 1H), 2.43 (m, 1H), 1.84 (m, 1H), 1.58 (m, 1H). MS (APCI+) m/z 298 (M+H)+.

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was triturated with diethyl ether
  6. filtrationthe solid collected by suction filtration

Sources & evidence

ORD record
ord-0df89bc867e24a40ac0ba7eb3451fc65
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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