(S)-6-hydroxymethyl-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one → (R)-2-Phenoxymethyl-6-trimethylsilanyloxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one

HRID 2046191Notes

Reaction equation

HRID 2046191 reaction equation
C(OC(N1[C@H](CN2C(C(OCC)=O)=CC(COC3C=CC=CC=3)=N2)COC1(C)C)=O)(C)(C)C.OC[C@@H]1CN2N=C(COC3C=CC=CC=3)C=C2C(=O)N1.[O:54]([CH2:61][C:62]1[CH:77]=[C:65]2[C:66](=[O:76])[NH:67][C@H:68]([CH2:70][O:71][Si:72]([CH3:75])([CH3:74])[CH3:73])[CH2:69][N:64]2[N:63]=1)[C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1>>[O:54]([CH2:61][C:62]1[CH:77]=[C:65]2[C:66](=[O:76])[NH:67][C@@H:68]([CH2:70][O:71][Si:72]([CH3:73])([CH3:75])[CH3:74])[CH2:69][N:64]2[N:63]=1)[C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1

Participants

4

Reactant 3

HCID 67974237(S)-6-hydroxymethyl-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-oneHCID 67976039HCID 67976039, compoundHCID 70654332(R)-4-(5-ethoxycarbonyl-3-phenoxymethyl-pyrazol-1-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 70654437(R)-2-Phenoxymethyl-6-trimethylsilanyloxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one

Procedure

The compound was prepared from (R)-4-(5-ethoxycarbonyl-3-phenoxymethyl-pyrazol-1-ylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester using the methods described in the preceding examples 31 ((S)-6-hydroxymethyl-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one) and 32 ((S)-2-phenoxymethyl-6-trimethylsilanyloxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one).

Sources & evidence

ORD record
ord-3730b334cb7d4ef7a2d4332e0584ff8f
Source dataset
uspto-grants-2013_11
Patent number
US08592422B2

Reaction notes

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