HCID 68291457, compound → HCID 10704451, compound

HRID 877844Notes

Reaction equation

HRID 877844 reaction equation
C([N:8]1[CH2:15][C@@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]2([CH2:13][CH2:12][CH2:11]2)[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH2:13]1[C:10]2([C@H:14]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:15][NH:8][CH2:9]2)[CH2:11][CH2:12]1

Participants

5

Reactant 2

HCID 68291457HCID 68291457, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 10704451HCID 10704451, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A stirred solution of (S)-tert-butyl (6-benzyl-6-azaspiro[3.4]octan-8-yl)carbamate (enantiopure Intermediate 13, 0.364 g, 1.149 mmol) in Ethanol (21.3 mL) with Pd/C (10% b/w) (0.291 g, 2.73 mmol), was charged with hydrogen gas @ 50 psi in a pressure bottle and agitated for 4 hrs. +/−MS analysis after 3 hrs 15 min indicated that essentially no starting material remained (m/e 227.2, M+H for desired product). The catalyst was removed by filtration, and the filtrate was concentrated under vacuum to yield 0.247 g of the desired product as a tan oil. +/−MS: m/e 227.2 (M+H). 1H NMR (400 MHz, CHLOROFORM-d) δ 4.66 (br. s., 1H), 3.96 (br. s., 1H), 3.24 (dd, J=11.3, 6.1 Hz, 1H), 3.05 (d, J=11.0 Hz, 1H), 2.89 (d, J=11.2 Hz, 1H), 2.72 (dd, J=11.6, 3.4 Hz, 1H), 2.13 (dd, J=9.6, 3.4 Hz, 3H), 2.04-1.71 (m, 5H), 1.46 (s, 9H).

Workup

  1. wait+/−MS analysis after 3 hrs 15 min indicated

Sources & evidence

ORD record
ord-34e24aaacca841b688948e767b1a9324
Source dataset
uspto-grants-2015_03
Patent number
US08987268B2

Reaction notes

Loading…