Aluminium lithium hydride → HCID 68115513, compound

HRID 1503898Notes

Reaction equation

HRID 1503898 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[N:17]=[CH:18][N:19]=[C:20]3[C:27]=2[C:26]2[C@H:25]([CH2:28][C:29](OCC)=[O:30])[CH2:24][CH2:23][C:22]=2[S:21]3)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[OH:30][CH2:29][CH2:28][C@@H:25]1[CH2:24][CH2:23][C:22]2[S:21][C:20]3[C:27](=[C:16]([O:15][CH:12]4[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:14][CH2:13]4)[N:17]=[CH:18][N:19]=3)[C:26]1=2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 68115366HCID 68115366, compound

Product 1

HCID 68115513HCID 68115513, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 50-mL round-bottom flask containing 16.4 (180 mg, 0.38 mmol, 1.00 equiv) in distilled tetrahydrofuran (10 mL) was added LiAlH4 (30 mg, 0.79 mmol, 2.00 equiv) at 0° C. under nitrogen. The resulting solution was stirred for 30 min at room temperature. The reaction was then quenched with water and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate and concentrated under vacuum to afford tert-butyl N-(4-[[(3S)-3-(2-hydroxyethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(12),2(6),8,10-tetraen-12-yl]oxy]cyclohexyl)carbamate (16.5, 100 mg, 61%) as a yellow oil. MS: m/z 434 (M+H)+.

Workup

  1. customThe reaction was then quenched with water
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e19b05308dff46ef84c7049e1a3dd3c2
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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