HCID 86761366, compound → HCID 86761367, compound

HRID 1015513Notes

Reaction equation

HRID 1015513 reaction equation
C([O:8][CH2:9][C:10]12[CH2:18][CH:14]3[CH2:15][CH:16]([CH2:17]1)[C:12]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH2:13]3)[CH2:11]2)C1C=CC=CC=1>CO.[Pd]>[OH:8][CH2:9][C:10]12[CH2:18][CH:14]3[CH2:15][CH:16]([CH2:17]1)[C:12]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])([CH2:13]3)[CH2:11]2

Participants

4

Reactant 1

HCID 86761366HCID 86761366, compound

Product 1

HCID 86761367HCID 86761367, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred mixture of tert-butyl [1-(benzyloxymethyl)tricyclo[3.3.1.03,7]non-3-yl]carbamate (1.0 g, 2.8 mmol) obtained in step V in MeOH (11 mL), Pd/C (10%, 0.2 g) was added. The H2 pressure was then applied with the balloon for 2 h. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure to obtain tert-butyl [1-(hydroxymethyl)tricyclo[3.3.1.03,7]non-3-yl]carbamate as a viscous liquid (0.7 g) in 95% yield. m/z (M+1) 268; 1H NMR (CDCl3) 300 MHz δ 4.74 (s (br), 1H), 3.45 (s, 2H), 2.50-2.40 (m, 1H), 2.40-2.33 (m, 1H), 2.05-1.87 (m, 4H), 1.80 (dd, J=2.4, 10.3 Hz, 1H), 1.65 (dd, J=3.0, 10.0 Hz, 1H), 1.54-1.40 (m, 3H), 1.45 (s, 9H), 1.37 (dd, J=3.1, 10.0 Hz, 1H).

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0ddc59525c284f80a492af9d29c30b63
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

Loading…