(S)-(5-Isobutyl-indan-2-yl)-carbamic acid benzyl ester → (S)-5-Isobutyl-indan-2-ylamine

HRID 658344Notes

Reaction equation

HRID 658344 reaction equation
C(OC(=O)[NH:10][C@@H:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH:17]=2)[CH2:12]1)C1C=CC=CC=1>CO.[Pd]>[CH2:20]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[CH2:12][C@H:11]([NH2:10])[CH2:19]2)[CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 1

HCID 66744187(S)-(5-Isobutyl-indan-2-yl)-carbamic acid benzyl ester

Product 1

HCID 66745046(S)-5-Isobutyl-indan-2-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-(5-Isobutyl-indan-2-yl)-carbamic acid benzyl ester ( ) is dissolved in methanol (100 ml), 10% Pd—C (200 mg) is added and the flask is purged with H2(g) (0.35 bar). The reaction mixture is stirred for 18 hours, the catalyst is filtered off. The solvent is removed in vacuo to give title compound. 1H nmr (CDCl3, 400 MHz); 7.10 (d, 1H), 7.00 (s, 1H), 6.90 (d, 1H), 3.85 (m, 1H), 3.15 (dd, 2H), 2.65 (dt, 2H), 2.45 (d, 2H), 1.80 (br m, 3H), 0.90 (d, 6H).

Workup

  1. customthe flask is purged with H2(g) (0.35 bar)
  2. filtrationthe catalyst is filtered off
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-708b1d64f8ef48c5bba09818ad6390db
Source dataset
uspto-grants-2011_12
Patent number
US08076489B2

Reaction notes

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