Water → 3-(3-Azabicyclo[3.1.0]hexan-3-yl)propan-1-ol
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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]2C1(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]2To 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%).
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