Methanol → tert-butyl 1'-(8-(ethoxycarbonyl)-8-azabicyclo[3.2.1]octan-3-yl)-1H-spiro[isoquinoline-4,4'-piperidine]-2(3H)-carboxylate

HRID 296650Notes

Reaction equation

HRID 296650 reaction equation
[BH4-:44].[CH3:37][CH2:38][N:39]([CH2:40][CH3:41])[CH2:42][CH3:43].[CH3:51][OH:52].[CH3:53][CH:54]([CH3:55])[O-:56].[CH3:57][CH:58]([CH3:59])[O-:60].[CH3:61][CH:62]([CH3:63])[O-:64].[CH3:65][CH:66]([CH3:67])[O-:68].[Cl:48][CH2:49][Cl:50].[NH:1]1[CH2:2][CH2:3][C:4]2([CH2:5][N:6]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]32)[CH2:21][CH2:22]1.[Na+:45].[Na+:47].[O:23]=[C:24]1[CH2:25][CH:26]2[CH2:27][CH2:28][CH:29]([CH2:30]1)[N:31]2[C:32](=[O:33])[O:34][CH2:35][CH3:36].[OH-:46].[Ti+4:69]>>[N:1]1([CH:24]2[CH2:25][CH:26]3[CH2:27][CH2:28][CH:29]([CH2:30]2)[N:31]3[C:32](=[O:33])[O:34][CH2:35][CH3:36])[CH2:2][CH2:3][C:4]2([CH2:5][N:6]([C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH2:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]32)[CH2:21][CH2:22]1

Participants

11

Reactant 10

HCID 887MethanolHCID 923Sodium ion2×HCID 961HydroxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 28123BorohydrideHCID 114942Titanium cation (4+)HCID 401882Ethyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 3260420Isopropanolate4×HCID 49760902tert-Butyl 1H-spiro[isoquinoline-4,4'-piperidine]-2(3H)-carboxylate

Product 1

HCID 58089822tert-butyl 1'-(8-(ethoxycarbonyl)-8-azabicyclo[3.2.1]octan-3-yl)-1H-spiro[isoquinoline-4,4'-piperidine]-2(3H)-carboxylate

Sources & evidence

ORD record
ord-7a2ae268884249eebf7cc79ca2f9b747
Source dataset
Training data from https://doi.org/10.1039/C8SC04228D (8/10)

Reaction notes

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