Aluminium lithium hydride → HCID 67385689, compound

HRID 2096646Notes

Reaction equation

HRID 2096646 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)[CH2:6][C:5]2([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:17]([O-])=[O:18].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1([CH2:12][CH2:11][CH2:10][O:9][CH2:8]1)[CH2:6][C:5]2([NH:20][C:21](=[O:22])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:17][OH:18]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86657455HCID 86657455, compound

Product 1

HCID 67385689HCID 67385689, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-4-(tert-butoxycarbonylamino)-2′,4′,5′,6′-tetrahydrospiro[chroman-2,3′-pyran]-4-carboxylate (314 mg, 0.69 mmol) in anhydrous THF (10 mL) at −78° C. under N2 atmosphere was added 1 M LAH (in THF, 1.4 mL, 1.4 mmol) dropwise. The mixture was stirred for 30 min at this temperature and then warmed to room temperature and stirred overnight. The reaction mixture was cooled to 0° C. and quenched with Na2SO4.H2O carefully, then stirred several hours. The reaction was filtered through a short pad of Celite and washed with THF. The filtrate was evaporated to give 165 mg of the desired product as colorless oil. MS ESI +ve m/z 428 (M+H)+.

Workup

  1. stirringstirred overnight
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched with Na2SO4.H2O carefully
  4. stirringstirred several hours
  5. filtrationThe reaction was filtered through a short pad of Celite
  6. washwashed with THF
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-9035859a014e4809867e4d452ba9ae84
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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