(S)-2-phenyl-3-tert-butyl-5-hydroxymethyloxazolidine → 2-(3-tert. Butylamino-2-acetoxypropoxy)-3-cyanopyridine

HRID 972734Notes

Reaction equation

HRID 972734 reaction equation
C1(C2[N:11](C(C)C)[CH2:10]C(CO)O2)C=CC=CC=1.C[C@H]1N(C(CC)C)CC(CO)[O:19]1.[CH:29]([N:32]1[CH2:36][CH:35]([CH2:37]O)OC1)([CH3:31])C.[C:39]1([C@H:45]2[N:49]([C:50]([CH3:53])([CH3:52])[CH3:51])[CH2:48][CH:47]([CH2:54][OH:55])[O:46]2)C=CC=CC=1>>[C:50]([NH:49][CH2:48][CH:47]([O:46][C:45](=[O:19])[CH3:39])[CH2:54][O:55][C:36]1[C:35]([C:10]#[N:11])=[CH:37][CH:31]=[CH:29][N:32]=1)([CH3:51])([CH3:52])[CH3:53]

Participants

5

Reactant 4

HCID 12296652(S)-2-phenyl-3-tert-butyl-5-hydroxymethyloxazolidineHCID 125661982-Phenyl-3-isopropyl-5-hydroxymethyloxazolidineHCID 213212873-Isopropyl-5-hydroxymethyloxazolidineHCID 131710938(S)-2-methyl-3-sec. butyl-5-hydroxymethyloxazolidine

Product 1

HCID 1317109372-(3-tert. Butylamino-2-acetoxypropoxy)-3-cyanopyridine

Procedure

Isopropyl or sec. butyl amino analogues of the compounds of the above examples are prepared by substituting suitable oxazolidines e.g. 2-phenyl-3-isopropyl-5-hydroxymethyloxazolidine, (S)-2-methyl-3-sec. butyl-5-hydroxymethyloxazolidine, 3-isopropyl-5-hydroxymethyloxazolidine for the (S)-2-phenyl-3-tert. butyl-5-hydroxymethyloxazolidine reactant.

Sources & evidence

ORD record
ord-ea3ecd972f3c4c1cb8daf722628683da
Source dataset
uspto-grants-1977_10
Patent number
US04053605

Reaction notes

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