(7R,8R)-N-benzyl-7-methyl-1,4-dioxaspiro[4.5]decan-8-amine → (7R,8R)-7-Methyl-1,4-dioxaspiro[4.5]decan-8-amine

HRID 1970978Notes

Reaction equation

HRID 1970978 reaction equation
C([NH:8][C@@H:9]1[CH2:18][CH2:17][C:12]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:11][C@H:10]1[CH3:19])C1C=CC=CC=1>CO.[Pd]>[CH3:19][C@H:10]1[C@H:9]([NH2:8])[CH2:18][CH2:17][C:12]2([O:13][CH2:14][CH2:15][O:16]2)[CH2:11]1

Participants

4

Reactant 1

HCID 59543152(7R,8R)-N-benzyl-7-methyl-1,4-dioxaspiro[4.5]decan-8-amine

Product 1

HCID 59543149(7R,8R)-7-Methyl-1,4-dioxaspiro[4.5]decan-8-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (7R,8R)—N-benzyl-7-methyl-1,4-dioxaspiro[4.5]decan-8-amine (640 mg, 2.4 mmol) and Pd/C (10%, 52 mg) in MeOH (50 mL) was left to stir under H2 (1 atm) overnight. The mixture was filtered through celite, and concentrated to afford the title compound. 1H NMR (600 MHz, CDCl3) δ 3.91 (m, 4H); 1.15-2.12 (series of m, 7H); 0.96 (d, 3H).

Workup

  1. waitwas left
  2. filtrationThe mixture was filtered through celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5b3f5bfa187543d7b7486c1d0ee848e4
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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