Water → 3-(3-Azabicyclo[3.1.0]hexan-3-yl)propan-1-ol

HRID 132824Notes

Reaction equation

HRID 132824 reaction equation
C1(C)C=CC=CC=1.[OH:8][CH2:9][CH2:10][CH2:11][N:12]1[C:17](=O)[CH:16]2[CH:14]([CH2:15]2)[C:13]1=O.O>C(OCC)C>[CH:14]12[CH2:15][CH:16]1[CH2:17][N:12]([CH2:11][CH2:10][CH2:9][OH:8])[CH2:13]2

Participants

5

Reactant 3

HCID 962WaterHCID 1140TolueneHCID 612069603-(3-Hydroxypropyl)-3-azabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 675275193-(3-Azabicyclo[3.1.0]hexan-3-yl)propan-1-olYield 82.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) solution of sodium dihydro-bis(2-methoxyethoxy)aluminate in toluene (70% in mass, 2.43 mL, 4.5 eq.) was added 3-(3-hydroxy-propyl)-3-azabicyclo[3.1.0]hexane-2,4-dione (example 5, step 1, 320 mg, 1.0 eq.) in diethyl ether (5 mL). The mixture was stirred 40 min at 0° C. and 4 h at reflux. Water was carefully added to and the white mixture was filtered on a dicalite pad. The filtrate was extracted with diethyl ether and the combined organic layers were dried over sodium sulfate, filtered and evaporated in vacuo, yielding 220 mg (78%) of the desired product as a purple liquid which was used without additional purification. MS (m/e): 143.1 (MH+, 100%).

Workup

  1. temperatureat reflux
  2. filtrationwas filtered on a dicalite pad
  3. extractionThe filtrate was extracted with diethyl ether
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-97b85aa2cc0344e988f0fcd0751e848d
Source dataset
uspto-grants-2008_06
Patent number
US07388095B2

Reaction notes

Loading…