Aluminium lithium hydride → HCID 86695227, compound

HRID 1504066Notes

Reaction equation

HRID 1504066 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[C:17]3[C:18]4[C@H:19]([CH2:29][C:30](OCC)=[O:31])[CH2:20][CH2:21][CH2:22][C:23]=4[S:24][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:31][CH2:30][CH2:29][C@H:19]1[C:18]2[C:17]3[C:16]([O:15][CH:12]4[CH2:13][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][CH2:11]4)=[N:28][CH:27]=[N:26][C:25]=3[S:24][C:23]=2[CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86695225HCID 86695225, compound

Product 1

HCID 86695227HCID 86695227, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-[(13S)-3-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-13-yl]acetate (800 mg, 1.63 mmol, 1.00 equiv) in THF (30 mL) in an ice/water bath under nitrogen was added LiAlH4 (121.2 mg, 3.20 mmol, 2.00 equiv). The resulting solution was stirred for 2 h at room temperature and quenched with water, extracted with ethyl acetate (80 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1) to give 490 mg (67%) of tert-butyl N-(4-[[(13S)-13-(2-hydroxyethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate as a colorless oil.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate (80 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9ff40b6fe69042f589eb13f027e028d2
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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