tert-Butyl Formate → tert-butyl 5-chloro-1-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

HRID 529098Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:22]3[C:23]4[C@H:30]([CH3:31])[CH2:29][C@@H:28]([O:32]C(=O)C5C=CC([N+]([O-])=O)=CC=5)[C:24]=4[N:25]=[CH:26][N:27]=3)[C:5]2=[CH:6][CH:7]=1.C(OC(C)(C)C)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:19])[CH3:20])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:22]3[C:23]4[C@H:30]([CH3:31])[CH2:29][C@@H:28]([OH:32])[C:24]=4[N:25]=[CH:26][N:27]=3)[C:5]2=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 61207tert-Butyl Formate

HCID 69811182tert-butyl 5-chloro-1-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Product 1

HCID 69812700tert-butyl 5-chloro-1-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

Procedure

tert-butyl 5-chloro-1-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate was prepared by the procedures described in Example 3, Step 12, substituting tert-butyl 5-chloro-1-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate with tert-butyl 5-chloro-1-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,3′-pyrrolidine]-1′-carboxylate. LCMS (APCI+) m/z 357.1 [M+H−Boc]+; Rt=3.86.

Sources & evidence

ORD record: ord-c3a33a1cd4f04eb4883e873e09beb152
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346805B2

Reaction notes

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