4-((Benzyloxy)methyl)spiro[2.5]octane → Spiro[2.5]octan-4-ylmethanol

HRID 1748174Notes

Reaction equation

HRID 1748174 reaction equation
C([O:8][CH2:9][CH:10]1[CH2:17][CH2:16][CH2:15][CH2:14][C:11]21[CH2:13][CH2:12]2)C1C=CC=CC=1.[H][H]>CO.CCOC(C)=O>[CH2:12]1[C:11]2([CH2:14][CH2:15][CH2:16][CH2:17][CH:10]2[CH2:9][OH:8])[CH2:13]1

Participants

4

Reactant 2

HCID 679839844-((Benzyloxy)methyl)spiro[2.5]octaneHCID 178418361HCID 178418361, compound

Product 1

HCID 68083958Spiro[2.5]octan-4-ylmethanol

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 4-((benzyloxy)methyl)spiro[2,5]-octane (0.42 g, 1.8 mmol) in a 5:1 MeOH-EtOAc (12 mL) Pd/C (0.05 g, 5 wt %, 50% wet Degussa type) was added. The flask was fitted with a balloon of hydrogen, and the heterogeneous reaction mixture was stirred for 2 hours under a hydrogen atmosphere at rt. The catalyst solids were filtered off and the filtrate was concentrated under vacuum to give the desired product spyri[2.5]octan-4-ylmethanol as clear oil. 1H NMR (400 MHz, CDCl3) δ 3.74-3.62 (m, 2H), 3.48 (d, J=5.2 Hz, 2H), 1.65-1.59 (m, 2H), 1.51-1.43 (m, 3H), 1.27-1.24 (m, 1H), 1.12-1.11 (m, 1H), 0.96-0.95 (m, 1H), 0.41-0.37 (m, 1H), 0.29-0.17 (m, 3H). MS m/z 123.1 (M−17+1).

Workup

  1. filtrationThe catalyst solids were filtered off
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-4e2d1d55598a48dd94eb745ec25fbde8
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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