Acetic Acid → (2S,4R,5R)-2-benzhydryl-5-[(1H-indol-5-ylmethyl)-amino]-tetrahydro-pyran-4-ol

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	Indole-5-carboxaldehyde	HCID 589040	—
Reactant	(2S,4R,5R)-5-amino-2-benzhydryl-tetrahydro-pyran-4-ol	HCID 11514718	—
Reactant	(2S)-2-benzhydryl-3,6-dihydro-2H-pyran	HCID 54762285	—
Product	(2S,4R,5R)-2-benzhydryl-5-[(1H-indol-5-ylmethyl)-amino]-tetrahydro-pyran-4-ol	HCID 11509832	—

Reaction Steps

(2S, 4R, 5R)-5-amino-2-benzhydryl-tetrahydropyran-4-ol 31a (0.03 g, 0.11 mmol) was reacted with 1H-indol-5-carbaldehyde (0.02 g, 0.11 mmol), glacial acetic acid (0.01 g, 0.11 mmol), and NaCNBH3 (0.01 g, 0.21 mmol) (Procedure C) to give (2S, 4R, 5R)-2-benzhydryl-5-[(1H-indol-5-ylmethyl)-amino]-tetrahydropyran-4-ol, (−)32b, 0.04 g (92%, [α]D=(−)69.90, c=1, Acetone).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07915433B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-fcebf134f4de4f238e96cccc520f0a30
Source note	uspto-grants-2011_03