(S)-4-[2-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester → [(S)-3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-hydroxymethyl-propyl]-carbamic acid benzyl ester

HRID 1261836Notes

Reaction equation

HRID 1261836 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@@H:15]([CH2:16][CH2:17][N:18]2[CH2:25][CH2:24][C:21]3([CH2:23][CH2:22]3)[C@H:20]([OH:26])[CH2:19]2)[CH2:14][O:13]C1(C)C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@H:15]([CH2:14][OH:13])[CH2:16][CH2:17][N:18]1[CH2:25][CH2:24][C:21]2([CH2:23][CH2:22]2)[C@H:20]([OH:26])[CH2:19]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 67080106(S)-4-[2-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Product 1

HCID 67079922[(S)-3-((S)-4-Hydroxy-6-aza-spiro[2.5]oct-6-yl)-1-hydroxymethyl-propyl]-carbamic acid benzyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of (S)-4-[2-((S)-4-hydroxy-6-aza-spiro[2.5]oct-6-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (5.00 g, 12.9 mmol) in MeOH/water 9:1 (50 mL) was stirred at room temperature in the presence of Amberlite® IR-120 resin (15.8 g). After 16 h the resin was collected by filtration and washed with MeOH. The filtrate was discarded, and the product was recovered by digesting the Amberlite® resin three times in 7 M methanolic ammonia solution (60 mL) at room temperature over 15 min. The ammonia solutions were combined and evaporated to afford the title compound (4.27 g, 95%). Colourless oil, MS (ISP)=349.3 (M+H)+.

Workup

  1. filtrationAfter 16 h the resin was collected by filtration
  2. washwashed with MeOH
  3. customthe product was recovered
  4. customat room temperature
  5. customover 15 min
  6. customevaporated

Sources & evidence

ORD record
ord-687c7543d2cf445b817b61f6a331f4ad
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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