Ammonium Chloride → HCID 53793418, compound

HRID 654879Notes

Reaction equation

HRID 654879 reaction equation
[CH:1]1([CH2:7][C@H:8]2[C@H:12]([CH:13]=[O:14])[O:11][C:10]([CH3:16])([CH3:15])[N:9]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH:25]1[CH2:28][CH2:27][CH2:26]1.[Mg].[Cl-].[NH4+]>O1CCCC1>[CH:1]1([CH2:7][C@H:8]2[C@H:12]([C@H:13]([CH:25]3[CH2:28][CH2:27][CH2:26]3)[OH:14])[O:11][C:10]([CH3:16])([CH3:15])[N:9]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 78110BromocyclobutaneHCID 5462224MagnesiumHCID 14552357HCID 14552357, compound

Product 1

HCID 53793418HCID 53793418, compoundYield 28.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 7.23 g (22.2 mmol) of t-butyl (4S,5R)-4-(cyclohexylmethyl)-5-formyl-2,2-dimethyl-3-oxazolidinecarboxylate in 150 ml of tetrahydrofuran is added dropwise within 40 minutes at 30° to a solution of the Grignard compound prepared from 15 g (111 mmol) of bromocyclobutane and 2.7 g (111 mgram atom) of magnesium shavings in 150 ml of tetrahydrofuran and the reaction mixture is subsequently stirred at room temperature overnight. Thereafter, the reaction mixture is poured into 300 ml of a saturated ammonium chloride solution and extracted three times with 600 ml of ether each time. The ether extracts are washed with ammonium chloride solution, dried, filtered and evaporated. The crude product (9.34 g) is chromatographed on 500 g of silica gel with a 92.5:7.5 mixture of toluene and ethyl acetate as the eluting agent, whereby there are obtained 2.44 g of t-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(S)-cyclobutylhydroxymethyl]-2,2-dimethyl-3-oxazolidinecarboxylate as an oil, MS: 381 (M)+, and 2.9 g of the epimeric compound t-butyl (4S,5R)-4-(cyclohexYlmethyl)-5-[(R)-cyclobutylhydroxymethyl]-2,2-dimethyl-3-oxazolidinecarboxylate, likewise as an oil, MS: 381 (M)+.

Workup

  1. extractionextracted three times with 600 ml of ether each time
  2. washThe ether extracts are washed with ammonium chloride solution
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product (9.34 g) is chromatographed on 500 g of silica gel with a 92.5:7.5 mixture of toluene and ethyl acetate as the eluting agent, whereby there

Sources & evidence

ORD record
ord-30f0cc2f2de541b89e0f93f4c595f9af
Source dataset
uspto-grants-1992_07
Patent number
US05134123

Reaction notes

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