Sodium Sulfate → HCID 86682919, compound

HRID 1522901Notes

Reaction equation

HRID 1522901 reaction equation
C([O:4][CH2:5][C@@H:6]([N:8]1[C:13](=O)[CH:12]2[CH:10]([CH2:11]2)[C:9]1=O)[CH3:7])(=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C(OCC)C>[CH:10]12[CH2:11][CH:12]1[CH2:13][N:8]([C@@H:6]([CH3:7])[CH2:5][OH:4])[CH2:9]2

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86682920HCID 86682920, compound

Product 1

HCID 86682919HCID 86682919, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

A solution of (2S)-2-(2,4-dioxo-3-azabicyclo[3.1.0]hexan-3-yl)propyl acetate (485 mg, 2.3 mmol) and anhydrous diethyl ether (3 mL) was added over 5 min to a suspension of LiAlH4 (262 mg, 6.9 mmol) and anhydrous diethyl ether (20 mL) at rt under N2 (water bath used to control exotherm). After ˜9 h, anhydrous diethyl ether (10 mL) was added. After 24 h, Na2SO4*10H2O was added one crystal at a time until the bubbling ceased. The mixture was diluted with diethyl ether (50 mL) and filtered through Celite with additional diethyl ether (100 mL). The filtrate was concentrated and purified by silica gel chromatography (10:7; ethyl acetate:hexanes→10:7:2:1; ethyl acetate:hexanes:methanol:triethylamine) to give 220 mg of (2S)-2-(3-azabicyclo[3.1.0]hexan-3-yl)propan-1-ol. 1H NMR (DMSO-d6): δ 4.26 (t, 1H), 3.42 (m, 1H), 3.13 (ddd, 1H), 2.91 (d, 1H), 2.85 (d, 1H), 2.39-2.28 (m, 3H), 1.31 (m, 2H), 0.93 (d, 3H), 0.54 (m, 1H), 0.25 (m, 1H); MS: 142.2 (M+H)+.

Workup

  1. waitAfter 24 h
  2. filtrationfiltered through Celite with additional diethyl ether (100 mL)
  3. concentrationThe filtrate was concentrated
  4. custompurified by silica gel chromatography (10:7; ethyl acetate:hexanes→10:7:2:1; ethyl acetate:hexanes:methanol:triethylamine)

Sources & evidence

ORD record
ord-954d0afbf5ba45c6b17dbddda08d56ec
Source dataset
uspto-grants-2015_07
Patent number
US09078871B2

Reaction notes

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