3-(1,1-Dimethylethyl)-2-phenyloxazolidine-5-methanol → HCID 21388034, compound

HRID 1833877Notes

Reaction equation

HRID 1833877 reaction equation
[K].Cl[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[C:6]([CH3:14])=[CH:5][N:4]=1.ClC1C2C(=CC=C(Cl)C=2)C=C(C)N=1.[C:28]([N:32]1[CH2:36][CH:35]([CH2:37][OH:38])[O:34][CH:33]1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([CH3:31])([CH3:30])[CH3:29]>C(O)(C)(C)C>[C:28]([N:32]1[CH2:36][CH:35]([CH2:37][O:38][C:3]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([Cl:13])[CH:11]=3)[C:6]([CH3:14])=[CH:5][N:4]=2)[O:34][CH:33]1[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

6

Reactant 4

HCID 1088103-(1,1-Dimethylethyl)-2-phenyloxazolidine-5-methanolHCID 5462222PotassiumHCID 21388031HCID 21388031, compoundHCID 213880331,7-Dichloro-3-methylisoquinoline

Product 1

HCID 21388034HCID 21388034, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

0.74 g of Potassium is dissolved in 15 ml of absolute tert.-butanol and 4.0 g of 1,7-dichloro-4-methylisoquinoline [m.p. 90°-92°: preparable in manner analogous to that described in Helv. Chim. Acta 52 (1969) 1755-1762 for the preparation of 1,7-dichloro-3-methylisoquinoline] and 4.4 g of 3-tert.-butyl-5-hydroxymethyl-2-phenyloxazolidine are added. The solution is heated to 50° for 1 hour, whereupon it is evaporated to dryness. The product is digested in water, extracted with ether, the ether phase dried and the ether distilled off. 1-(3-tert.-Butyl-2-phenyl-5-oxazolidinyl-methoxy)-7-chloro-4-methylisoquinoline is obtained as an oil.

Workup

  1. additionare added
  2. temperatureThe solution is heated to 50° for 1 hour, whereupon it
  3. customis evaporated to dryness
  4. extractionextracted with ether
  5. dry with materialthe ether phase dried
  6. distillationthe ether distilled off

Sources & evidence

ORD record
ord-af7997618c58455197bca9e386e3403a
Source dataset
uspto-grants-1978_01
Patent number
US04067873

Reaction notes

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