HCID 123811958, compound → HCID 66981875, compound

HRID 712806Notes

Reaction equation

HRID 712806 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[CH2:25][CH:24]2[CH:22]([CH2:23]2)[N:21]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>[OH:18][CH2:19][CH:20]1[CH2:25][CH:24]2[CH:22]([CH2:23]2)[N:21]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27]

Participants

4

Reactant 1

HCID 123811958HCID 123811958, compound

Product 1

HCID 66981875HCID 66981875, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

To a solution of (3R)-tert-butyl 3-(((tert-butyldiphenylsilyl)oxy)methyl)-2-azabicyclo[3.1.0]hexane-2-carboxylate (D31) (2.1 g, 4.6 mmol) in THF (130 ml), TBAF 1M sol in THF (9.2 ml) was added and the solution was stirred at RT for 18 hours. Solvent was evaporated and the residue purified by Biotage SNAP-Si column (50 g), eluting with DCM/Et2O from 100/0 to 80/20. Collected fractions after solvent evaporation afforded the title compound (D32) (490 mg).

Workup

  1. additionwas added
  2. customSolvent was evaporated
  3. customthe residue purified by Biotage SNAP-Si column (50 g)
  4. washeluting with DCM/Et2O from 100/0 to 80/20
  5. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-27e159daa6e44ca0ba865117cb365e7d
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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