Hydrochloric Acid → 2-Amino-2-methyl-3-prop-2-ynyloxy-propan-1-ol

HRID 1962875Notes

Reaction equation

HRID 1962875 reaction equation
[CH3:1][C:2]1([CH2:12][O:13]CC#C)[NH:6][C:5]2(CCC[CH2:8][CH2:7]2)[O:4][CH2:3]1.Cl>O>[NH2:6][C:2]([CH3:1])([CH2:3][O:4][CH2:5][C:7]#[CH:8])[CH2:12][OH:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 595654083-Methyl-3-prop-2-ynyloxymethyl-1-oxa-4-aza-spiro[4.5]decane

Product 1

HCID 595653842-Amino-2-methyl-3-prop-2-ynyloxy-propan-1-olYield 102.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Methyl-3-prop-2-ynyloxymethyl-1-oxa-4-aza-spiro[4.5]decane (1.83 g) in an aqueous solution of HCl (6N) (2.73 ml) were refluxed for 1 hr. The reaction mixture was cooled down to room temperature, diluted with water and extracted thrice with ethyl ether. The two layers were separated. The aqueous layer was concentrated under reduced pressure to yield 2-amino-2-methyl-3-prop-2-ynyloxy-propan-1-ol hydrochloric salt (1.205 g) as a white beige solid which was used as such in Stage 3 described below. 1H NMR (DMSO) δ ppm: 8.02 (3H, s br); 5.47 (1H, s br); 4.21 (2H, s); 3.54-3.49 (5H, m); 1.15 (3H, s).

Workup

  1. extractionextracted thrice with ethyl ether
  2. customThe two layers were separated
  3. concentrationThe aqueous layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae3bb24121ea4854a6d21cbb4a62e16d
Source dataset
uspto-grants-2013_04
Patent number
US08415272B2

Reaction notes

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