3-Hydroxyazetidine hydrochloride → HCID 86708505, compound

HRID 1430828Notes

Reaction equation

HRID 1430828 reaction equation
[O:1]1[CH2:4][C:3](=O)[CH2:2]1.Cl.[NH:7]1[CH2:10][CH:9]([OH:11])[CH2:8]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[O:1]1[CH2:2][CH:3]([N:7]2[CH2:10][CH:9]([OH:11])[CH2:8]2)[CH2:4]1

Participants

5

Reactant 3

HCID 27592903-Hydroxyazetidine hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-Oxetanone

Product 1

HCID 86708505HCID 86708505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of oxetan-3-one (0.5 g, 6.94 mmol), azetidin-3-ol hydrochloride (1.140 g, 10.41 mmol) and 4 A molecular sieves (1.5 g) in dichloromethane (10 mL) was stirred at room temperature for 4 h. sodium triacetoxyborohydride (2.94 g, 13.88 mmol) was added and the reaction mixture was stirred at room temperature overnight. The ppt was filtered through a pad of celite and the filtrate was diluted with ethyl acetate (more ppt appeared) and filtered again. The filtrate was concentrated in vacuo and the crude product was purified by flash chromatography on silica gel using an automated ISCO system (80 g column, eluting with 3-10% 2N ammonia in methanol/dichloromethane). 1-(oxetan-3-yl)azetidin-3-ol was obtained as a colorless oil.

Workup

  1. additionwas added
  2. filtrationThe ppt was filtered through a pad of celite
  3. additionthe filtrate was diluted with ethyl acetate (
  4. filtrationfiltered again
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe crude product was purified by flash chromatography on silica gel using
  7. washan automated ISCO system (80 g column, eluting with 3-10% 2N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-743fe627af7c430a8591f792e19615ef
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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