Aluminium lithium hydride → (2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methanamine

HRID 1848013Notes

Reaction equation

HRID 1848013 reaction equation
[CH3:1][C:2]1([CH3:22])[N:6]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[C@@H:5]2[CH2:18][CH2:19][CH2:20][CH2:21][C@H:4]2[O:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][C:2]1([CH3:22])[N:6]([C:7]2[S:8][C:9]3[CH:15]=[C:14]([CH2:16][NH2:17])[CH:13]=[CH:12][C:10]=3[N:11]=2)[C@@H:5]2[CH2:18][CH2:19][CH2:20][CH2:21][C@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866810332-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazole-6-carbonitrile

Product 1

HCID 86681035(2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methanamineYield 93.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred mixture of 2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazole-6-carbonitrile (260 mg, 0.8 mmol) from Step 3 of this Example in THF (10 mL) at 0° C. was added LAH (3.3 mL of a 1M solution in THF, 3.3 mmol). The mixture was allowed to warm slowly to rt and stirred for 15 h. The mixture was again cooled to 0° C. and Na2SO4.10H2O was added slowly. The mixture was stirred for 2 h, filtered, and the filtrate was concentrated under reduced pressure to afford (2-((3aR,7aR)-2,2-dimethylhexahydrobenzo[d]oxazol-3(2H)-yl)benzo[d]thiazol-6-yl)methanamine (237 mg). The material was used in the next step without further purification. LCMS (ESI) m/z 318 (M+H)+.

Workup

  1. customat 0° C.
  2. temperatureThe mixture was again cooled to 0° C.
  3. stirringThe mixture was stirred for 2 h
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e566092d75004d80a78507e12c404248
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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