Diisobutylaluminumhydride → (4R,9aR)-6-Cyclopropylmethoxymethyl-7-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 1272150Notes

Reaction equation

HRID 1272150 reaction equation
CCOC(C1N(C(OC(C)(C)C)=O)C2=NC=C(OC(=O)C3C=CC=CC=3)C=C2C=1)=O.C[O:32][C:33]([C:35]1[CH:47]=[C:46]2[C:38]([N:39]3[C@H:44]([CH2:45]2)[CH2:43][N:42]([C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])[CH2:41][C@H:40]3[CH3:55])=[N:37][C:36]=1[CH2:56][O:57][CH2:58][CH:59]1[CH2:61][CH2:60]1)=O.[H-].C([Al+]CC(C)C)C(C)C>>[C:51]([O:50][C:48]([N:42]1[CH2:41][C@@H:40]([CH3:55])[N:39]2[C@H:44]([CH2:45][C:46]3[C:38]2=[N:37][C:36]([CH2:56][O:57][CH2:58][CH:59]2[CH2:60][CH2:61]2)=[C:35]([CH2:33][OH:32])[CH:47]=3)[CH2:43]1)=[O:49])([CH3:52])([CH3:53])[CH3:54]

Participants

4

Reactant 3

HCID 21225700DiisobutylaluminumhydrideHCID 693563741H-Pyrrolo[2,3-b]pyridine-1,2-dicarboxylic acid, 5-(benzoyloxy)-, 1-(1,1-dimethylethyl) 2-ethyl esterHCID 69361749(4R,9aR)-6-Cyclopropylmethoxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2,7-dicarboxylic acid 2-tert-butyl ester 7-methyl ester

Product 1

HCID 69359857(4R,9aR)-6-Cyclopropylmethoxymethyl-7-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Procedure

This compound was prepared in analogy to example 35, intermediate c) from (4R,9aR)-6-cyclopropylmethoxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2,7-dicarboxylic acid 2-tert-butyl ester 7-methyl ester and diisobutylaluminium hydride.

Sources & evidence

ORD record
ord-25bf81aa189e4b60a5fbf422b523e714
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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